Glycyl-L-proline

Ganapathy, V. and F. H. Leibach. Role of pH gradient and membrane potential in dipeptide transport in intestinal and renal brush-border membrane vesicles from the rabbit. Studies with L-camosine and glycyl-L-proline. J. Biol. Chem. 1983, 258, 14189-14192. 

Glycyl-L-proline [704-15-4] M 172.2, m 185. Crystd from water at 50-60° by addition of EtOH. 

Several different types of chiral additives have been used including (IR)-(-)-ammonium-IO-camphorsulfonic acid, cyclodextrins. proteins, and various amino acid derivatives such as //-benzoxycarbonyl-glycyl-L-proline as well as macrocyclic antibiotics. 

Fig. 3.10 Possible three points of interaction between N-benzoxy-glycyl-l-proline, ZGP, and propranolol. There will be a strong attraction between the acidic functional group of the chiral selector and the amino-group of the analyte and a potential H-bonding interaction between a carbonyl group of the ZGP and the hydroxyl group of the propranolol. A third interaction is possibly a rc-stacking interaction, or steric repulsion, between the naphthalene ring of propranolol and the benzene ring of the ZGP.

Karlsson, A. Pettersson, C. Enantiomeric separation of amines using A-benzoxycarbonyl-glycyl-L-proline as chiral additive and porous graphitic carbon as solid phase. J. Chromatogr. A, 1991, 543, 287-297. 

Plates HPTLC silica gel plates HP-KF. Whatman, USA Eluents methylene chloride-methanol, 75 25 (v/v) + different amounts of A/-benzoxycarbonyl-alanyl-L-prolinc (ZAP). /V-benzoxycarbonyl-isolcucyl-L-proline (ZIP). A-benzoxycarbonyl-L-proline (ZP), N-bcnzoxycarbonyl-glycyl-L-proline (ZGP), (IR)-(-)-ammonium-lO-cumphersulfonate (CSA) or/and tricthy-laminc (TEA) (sec ref.)... 

Eluent dichloromethane contg. 5 mM N-benzoxycarbonyl-glycyl-L-proline (ZGP)... 

C2 6H oNi 06, L-Prolyl-L-tyrosy 1-L-isoleucyl-L-leucine, 45B, 532 C2 sHu 3N5O10 f N-Benzyloxycarbonyl-glycyl-L-prolyl-L-leucyl-glycyl-L-proline dihydrate, 44B, 445 C28H47N3O6, Majusculamide B hydrate, 43B, 621... 

C32H48BrNsOi1, o-Bromocarbobenzoxy-glycyl-L-prolyl-L-leucyl-glycyl-L-proline ethyl acetate monohydrate, 37B, 279 C33H57N3O9, Enniatin B, 43B, 622... 

Plates DIOL F 254 HPTLC plates, Merck, Germany Eluent dichloromethane contg. 0.4 mM ethanolamine and 5 mM N-caibobenzoxy glycyl-L-proline Visualization UV (280 or 300 nm)... 

Enantiomers of phenylpropanolamine, octopamine, pindolol, norphenyl-ephedrine, propanolol, and isoproterenol were separated with Rf differences of 0.05-0.24 by development of Whatman HP-KF HPTLC plates with dichloro-methane/methanol (75 25) containing different amounts of A-benzoxycarbonyl (BOC)-alanyl-L-proline (ZAP), BOC-isoleucyl-L-proline (ZIP), BOC-L-proline (ZP), BOC-glycyl-L-proline (ZGP), (lR)-(—)-ammonium-10-camphorsulfonate (CSA), and triethylamine (TEA). Visualization was under 254 nm UV light [29]. 

Antipodes of /3-blockers were discriminated using only in one case /3-CD [23] and more often chiral counter-ions such as (lR)-(-)-ammonium-10-camphorsulfonate (CSA), A-carbobenzyloxy-glycyl-L-proline (ZGP), and various... 

Enantiomers of metoprolol were separated on LiChrosorb Diol HP-TLC plates with dichloromethane and A/-benzoxycarbonyl-glycyl-L-proline as chiral selectors added to the mobile phase. The experiments revealed that saturation of the chromatographic system with water has a beneficial effect on chromatographic separation and reproducibility [20]. 

Mobile phase A-benzoxycarbonyl-glycyl-L-proline in dichloromethane at a concentration 5 mmol/1. 

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